Synthetic Approaches To Non-Symmetric Bodipy Dyes: Working Toward Small Molecular Sensors For Detection Of Amyloids

Abstract

BODIPY dyes are versatile sensors because of their many desirable photophysical properties. These dyes have been shown to be viable probes for detecting amyloid -beta peptides, while showing significant advantages over currently utilized dye-binding assays. Most of the research and development of these dyes has been done on symmetric compounds, and current syntheses of non-symmetric dyes are neither facile nor efficient. Our research has examined ways to synthesize non-symmetric BODIPY dyes more efficiently using a solvent-free, one-pot synthetic approach. By grinding a pyrrole and a carbonyl-containing pyrrole in the presence of a base, followed by the addition of boron trifluoride, we have synthesized non-symmetric BODIPY dyes in a more expeditious manner. Our current synthetic methods appear to be applicable to a variety of structurally and functionally diverse BODIPY dyes, although the overall efficiency still needs improvements. Based on the initial success, it is anticipated that a facile, efficient and economical synthetic approach toward non-symmetric BODIPY dyes will be achieved in the near future.